NPASS Compound

Natural Product: NPC221110

Natural Product ID	NPC221110
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Saikosaponin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3542194
PubChem CID	167928
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 123130 0 0 0 0 0 0 0 0999 V2000 11.3272 -0.5692 1.1789 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5282 -0.9627 -0.1421 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1842 -1.3733 -0.7206 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3253 -0.2846 -0.6544 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0927 -0.7131 -1.2052 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1072 0.1460 -0.7493 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1344 -0.4948 0.0158 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8026 -0.2765 -0.6298 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7802 -1.1517 -1.7480 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6305 -0.5084 0.2622 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1038 -0.8310 1.5918 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9123 0.1361 2.1058 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2291 0.1193 1.3948 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7634 1.3996 1.3782 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3644 1.5223 2.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 0.5563 0.3920 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4759 0.4002 0.3209 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8790 0.3906 1.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5717 -0.0071 1.5993 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3468 1.1121 0.8890 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7539 1.1380 -0.4824 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7159 1.2464 -0.6380 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2382 2.6535 -0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 0.6440 -2.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3874 0.7090 -2.2691 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5774 1.9566 -1.4474 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9307 1.2572 -1.5080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6566 1.3413 -0.1801 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7755 0.6321 0.8041 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3760 0.4411 2.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6685 0.3793 2.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5807 0.4926 1.1234 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9638 0.5832 -0.2267 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7866 -0.6979 -0.9825 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0053 1.3221 -1.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3087 0.5283 -1.0307 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7072 0.2173 0.3590 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7206 -0.4284 1.2787 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5588 -1.8571 1.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8414 -2.5816 0.9476 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7345 -3.1839 -0.4586 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0581 -3.8101 1.8540 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0643 -1.7437 1.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0371 -0.3858 0.5275 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5771 1.6100 1.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2627 1.7294 1.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2822 1.4857 -1.4657 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8859 2.7789 0.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2785 2.2984 1.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1830 -0.5873 -2.7056 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6425 -0.7582 -3.0833 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3231 -1.7640 -2.1783 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6578 -2.9847 -2.3620 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2583 0.4773 -3.1054 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4107 -1.6221 -3.2566 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5704 0.0811 1.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9330 -0.1390 -0.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1869 -1.8574 -0.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7460 -2.1867 -0.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8948 -1.7325 -0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3911 -1.5692 0.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8395 0.7532 -1.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1278 -1.8585 -1.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1551 -1.4745 0.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0843 -0.1601 3.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9292 -0.5212 1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6502 1.3078 0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0647 2.1098 2.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3870 1.6048 2.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4311 2.0657 1.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3099 -0.6593 0.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3904 -0.4384 2.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0535 1.2963 2.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0146 -0.3420 2.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5686 -0.8555 0.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9715 0.0749 -0.8521 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0979 3.2863 0.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8924 3.0594 -1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3619 2.5686 -0.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5721 1.3217 -2.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6664 -0.3969 -2.0777 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5794 0.9324 -3.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5891 3.0111 -1.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 1.8049 -2.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4742 1.6893 -2.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6056 0.1883 -1.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6600 -0.4199 0.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7369 0.3620 3.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0993 0.2364 3.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7696 -1.1995 -1.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0431 -1.3906 -0.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5056 -0.3774 -2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2430 2.3064 -0.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6645 1.3955 -2.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3996 -0.2440 -1.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1418 -0.1497 2.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6942 -2.3408 0.8250 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3612 -2.2088 2.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3200 -4.1195 -0.5321 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6567 -3.3758 -0.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0920 -2.4618 -1.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3208 -4.5828 1.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9878 -3.4837 2.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0966 -4.1397 1.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9052 -2.3085 0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3454 -1.7172 2.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6386 0.2853 1.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5822 -0.3426 -0.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0252 2.3885 0.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1601 1.4706 1.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0692 1.6259 -2.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4540 3.0751 0.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9834 3.4193 0.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4380 3.1827 -0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6870 2.1797 2.7033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3024 2.5259 2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9451 3.2456 1.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8048 0.3725 -3.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6510 -1.2095 -4.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3779 -1.8337 -2.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7933 -3.6137 -1.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4931 0.7151 -4.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2857 -2.3581 -2.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 10 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 6 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 40 43 1 0 43 44 1 0 37 45 1 1 45 46 1 0 36 47 1 0 28 48 1 1 20 49 1 1 5 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 52 3 1 0 13 7 1 0 22 17 1 0 33 28 1 0 44 37 1 0 29 20 1 0 32 46 1 1 38 32 1 0 1 56 1 0 2 57 1 0 2 58 1 0 3 59 1 1 5 60 1 6 7 61 1 1 8 62 1 6 9 63 1 0 10 64 1 6 12 65 1 1 13 66 1 1 14 67 1 0 15 68 1 0 15 69 1 0 15 70 1 0 17 71 1 6 18 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 21 76 1 6 23 77 1 0 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 27 85 1 0 27 86 1 0 29 87 1 6 30 88 1 0 31 89 1 0 34 90 1 0 34 91 1 0 34 92 1 0 35 93 1 0 35 94 1 0 36 95 1 6 38 96 1 1 39 97 1 0 39 98 1 0 41 99 1 0 41100 1 0 41101 1 0 42102 1 0 42103 1 0 42104 1 0 43105 1 0 43106 1 0 44107 1 0 44108 1 0 45109 1 0 45110 1 0 47111 1 0 48112 1 0 48113 1 0 48114 1 0 49115 1 0 49116 1 0 49117 1 0 50118 1 1 51119 1 6 52120 1 6 53121 1 0 54122 1 0 55123 1 0 M END

Standard InCHIKey	KYWSCMDFVARMPN-MSSMMRRTSA-N
Standard InCHI	InChI=1S/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21-,22-,23-,24-,25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@@H]2O)C)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3C=C[C@]34[C@@]2(C)C[C@@H]([C@@]2([C@H]4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	780.47	Volume:	778.173 ? Van der Waals volume.
Dense:	1.003	LogP:	0.804 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.333 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.669 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	41.0
TPSA:	207.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.143	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.259	Fsp³:	0.952
MCE-18:	225.366 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.809	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.367	MDCK Permeability:	-5.03
Pgp-inhibitor:	0.011	Pgp-substrate:	0.096
PAMPA:	0.99 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.036	30% Bioavailability (F30%):	0.648
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.033
Plasma Protein Binding (PPB):	78.816%	Volume Distribution (VD):	-0.49
Fu:	17.873% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.02
BSEP inhibitor:	0.902

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.13	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.259
HLM stability:	0.755 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.934

Half-life (T1/2):

3.922

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.083
Human Hepatotoxicity (H-HT):	0.335	Drug-induced Liver Injury (DILI):	0.232
AMES Toxicity:	0.71	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.998
Carcinogencity:	0.373	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.071
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.991
Hematotoxicity:	0.123	Drug-induced Nephrotoxicity:	0.761
Genotoxicity:	0.039	RPMI-8226 Immunitoxicity:	0.161
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.263
BCF:	1.237 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.476 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.891 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.071 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO33140	physospermum verticillatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19467877]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33140	physospermum verticillatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	16
Activity	1
Retention_time	1

Activity Type	# Activity
Cell line	14
Unchecked	1
Non-molecular	2
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	101800.0	nM	PMID[19467877]
NPT492	Cell line	Caco-2	Homo sapiens	IC50	=	17900.0	nM	PMID[19467877]
NPT2287	Cell line	COR-L23	Homo sapiens	IC50	=	600.0	nM	PMID[19467877]
NPT81	Cell line	A549	Homo sapiens	IC50	=	17700.0	nM	PMID[19467877]
NPT858	Cell line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[19467877]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[19467877]
NPT2282	Cell line	C32	Homo sapiens	IC50	=	43500.0	nM	PMID[19467877]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	23900.0	nM	PMID[19467877]
NPT369	Cell line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[19467877]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[19467877]
NPT81	Cell line	A549	Homo sapiens	IC50	=	14540.0	nM	PMID[26259802]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	8340.0	nM	PMID[26259802]
NPT1872	Cell line	Bcap37	Homo sapiens	IC50	=	13960.0	nM	PMID[26259802]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	18990.0	nM	PMID[26259802]
NPT28438	Unchecked	Unchecked	n.a.	Activity	=	70.22	%	PMID[29353722]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[19467877]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	13010.0	nM	PMID[26259802]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Retention_time	=	39.9	min	PMID[23277344]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC221110 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24983
0.1-0.2	21445
0.2-0.3	2633
0.3-0.4	670
0.4-0.5	98
0.5-0.6	12
0.6-0.7	2
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180459
1.0	High Similarity	NPC195116
0.9091	High Similarity	NPC600293
0.9059	High Similarity	NPC285253
0.9	High Similarity	NPC476305
0.8652	High Similarity	NPC473128
0.8462	Intermediate Similarity	NPC40133
0.8462	Intermediate Similarity	NPC49413
0.8202	Intermediate Similarity	NPC290608
0.8193	Intermediate Similarity	NPC38376
0.8193	Intermediate Similarity	NPC80210
0.7957	Intermediate Similarity	NPC44298
0.7826	Intermediate Similarity	NPC473130
0.7826	Intermediate Similarity	NPC110494
0.6923	Remote Similarity	NPC473125
0.6869	Remote Similarity	NPC157474
0.596	Remote Similarity	NPC109792
0.596	Remote Similarity	NPC57065
0.596	Remote Similarity	NPC54521
0.5862	Remote Similarity	NPC92885
0.5784	Remote Similarity	NPC473127
0.5784	Remote Similarity	NPC110656
0.5743	Remote Similarity	NPC162354
0.5534	Remote Similarity	NPC473126
0.5315	Remote Similarity	NPC257964
0.5283	Remote Similarity	NPC203354
0.5263	Remote Similarity	NPC471373
0.5046	Remote Similarity	NPC18724

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC221110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7682
0.1-0.2	1411
0.2-0.3	54
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data